Profile

Shay Weiss | Product Engineering & Enterprise AI Transformation Leader

Executive Profile

I am a Dublin-based Product Engineering and Enterprise AI Transformation leader with 20+ years across Engineering, Product, DevOps, Architecture, Digital Platforms, Security, Governance, Enterprise Delivery and AI adoption.My strength is turning complex enterprise technology ambition into real operating capability. That means building teams, creating leadership rhythm, connecting product direction with engineering execution, improving delivery confidence, and helping organisations adopt AI in a way that is practical, governed and useful.I work best where technology, people, delivery, risk and business value meet.

At a Glance

Dublin, Ireland
20+ years in technology leadership
Product Engineering, Engineering Leadership and DevOps
Enterprise AI Transformation and AI adoption
Delivery governance and product health
LLM security, indirect prompt injection and RAG risk
WBA Technology Center Ireland | Novartis | Teva Pharmaceuticals
MSc in Artificial Intelligence, University of Limerick

Core Capabilities

Product Engineering Leadership

I build the operating model around product-engineering work: leadership structure, ownership, delivery rhythm, stakeholder confidence and the connection between product direction and engineering execution.

Enterprise AI Transformation

I help organisations move AI from fragmented experimentation into practical adoption, responsible use, onboarding, governance, use-case delivery and workforce capability.

Delivery Governance

I make complex delivery visible and executable. For me, governance is not reporting theatre. It should create clarity, decisions, ownership and action.

LLM Security & AI Risk

My MSc AI research focuses on LLM security, indirect prompt injection, RAG risk, enterprise AI assistant behaviour and the trust boundaries around generative AI systems.

Proof in Practice

Shay Weiss leading a product engineering and technology capability session at WBA Technology Center Ireland.

Product Engineering & Site Build

Building enterprise product-engineering capability

At WBA Technology Center Ireland, I joined during the early build phase and helped build Product, Engineering, DevOps / Delivery, UX and AI adoption capability from initial setup into a mature operating model.

The work included developing managers and functional leads, improving delivery governance, creating stakeholder confidence and connecting Ireland-based capability into wider enterprise delivery across Europe and the US.

The real work was not only managing people. It was building the machine around the work: leadership, culture, operating rhythm, governance and trust.

AI Day winners board at WBA Technology Center Ireland, showing practical AI adoption and team innovation.

Enterprise AI Adoption

Moving AI from experimentation into adoption

A major part of my recent work has been moving enterprise AI from scattered experimentation into structured adoption.

I initiated and sponsored an AI Community of Practice focused on education, responsible use, onboarding, governance, use cases, support and confidence-building across technical and non-technical teams.

For me, AI transformation is not a licence rollout. Access is not transformation. Real adoption happens when people learn how to use AI safely and practically in their actual work.

Shay Weiss holding MSc Artificial Intelligence research material focused on LLM security and indirect prompt injection.

MSc AI / LLM Security

Researching the hidden risk in enterprise AI

My MSc research in Artificial Intelligence focused on indirect prompt injection and indirect input attacks against LLM-based systems.

The core question was simple: can an enterprise AI system be manipulated by someone who never touches the model?

This work connects directly to enterprise AI adoption, especially as organisations rely more on AI assistants, RAG systems and agentic workflows.

Career Foundation

WBA Technology Center Ireland

Director-level leadership across Product Engineering, Engineering, DevOps / Delivery, UX, Enterprise AI adoption and delivery governance.

Built capability from early setup, led managers and functional leads, governed delivery across distributed enterprise teams, and supported business-critical pharmacy technology across large-scale store and fulfilment operations.

Novartis

Led global digital platform and engineering capability across enterprise digital channels, supporting internal and external platforms across global functions and markets.

The work covered web, mobile, social marketing platforms, content streaming, low-code development, digital asset management, AR / VR, software-as-a-medical-device engineering, architecture direction and delivery governance.

Teva Pharmaceuticals

Held progressive global technology leadership roles across DevOps, Architecture, Infrastructure, Product, Development and Digital Technology.

Built DevOps as a new enterprise service, introduced CI/CD and infrastructure-as-code capability, created unified digital architecture direction and supported complex global technology transformation.

Featured Public Work

Shay Weiss public LinkedIn post about enterprise AI risk, indirect prompt injection and RAG security.

The Hidden Risk in Enterprise AI

MSc AI research into indirect prompt injection, RAG risk and how enterprise AI systems can be manipulated through trusted-looking content.

Read LinkedIn Post

AI Across Digital and Physical Retail

Speaker Chair at Dublin Tech Summit, moderating a panel on next-generation retail experiences and the role of AI across digital and physical customer channels.

Read LinkedIn Post

Practical Enterprise AI Adoption

Work on moving enterprise AI from hype and experimentation into practical workforce capability, responsible use, onboarding and real business value.

Shay Weiss with WBA team members after Hell & Back, showing team culture and leadership in practice.

Team Culture in Practice

Leadership is not only slides and slogans. It is how people show up for each other when the work gets messy.

Read LinkedIn Post

Detailed Profile & FAQ

Who is Shay Weiss?

Shay Weiss is a Dublin-based Product Engineering and Enterprise AI Transformation leader with 20+ years of experience across Engineering, Product, DevOps, Architecture, Digital Platforms, Security, Governance, Enterprise Delivery and AI adoption.

What does Shay Weiss do?

Shay helps complex enterprises turn technology ambition into real operating capability. His work includes building teams, creating leadership rhythm, improving delivery confidence, connecting product direction with engineering execution and helping organisations adopt AI in a practical, governed and useful way.

What is Shay Weiss known for professionally?

Shay is known for building technology capability in complex enterprise environments. He creates order in ambiguity, builds leaders, improves delivery governance, connects product and engineering, and helps organisations turn AI from experimentation into practical adoption.

What kind of roles is Shay Weiss suited for?

Shay is suited for senior roles across Product Engineering leadership, Engineering leadership, Enterprise AI Transformation, AI Adoption, Technology Capability Building, Delivery Governance, Technology Centre leadership, Platform Engineering leadership and VP Engineering path roles.

What is Shay’s experience in Product Engineering?

Shay has led across Product Management, Engineering, DevOps / Delivery, UX and delivery governance. His work focuses on connecting product direction with engineering execution and building the operating rhythm needed for enterprise-scale delivery.

What is Shay’s experience in Enterprise AI Transformation?

Shay has led practical enterprise AI adoption work across technical and non-technical teams, including community building, education, responsible use, onboarding, support, use-case development and workforce enablement.

What is Shay’s AI research about?

Shay’s MSc AI research focuses on LLM security, indirect prompt injection, indirect input attacks, RAG risk, AI governance and enterprise AI assistant behaviour.

What is indirect prompt injection?

Indirect prompt injection is a risk where hidden or malicious instructions are placed inside content that an AI system later reads, retrieves or processes. The user may ask a normal question, but the AI may be influenced by instructions hidden inside documents, emails, webpages or knowledge sources.

Why does indirect prompt injection matter for enterprise AI?

Enterprise AI systems often read company documents, emails, webpages, SharePoint content, Google Drive content, knowledge bases and other sources. If those sources contain hidden or manipulated instructions, the AI output can become unreliable, unsafe or misleading.

What is Shay’s leadership style?

Shay’s leadership style is practical, people-first and execution-focused. He builds trust, creates clarity, develops managers and functional leads, protects teams from unhelpful noise and helps people take ownership in ambiguous environments.

What does Shay mean by delivery governance?

For Shay, delivery governance is not reporting theatre. It is the operating rhythm that makes product health, roadmap risk, release readiness, security visibility, capacity, ownership and decision-making clear enough for teams and stakeholders to act.

What industries has Shay worked in?

Shay has worked across pharmaceuticals, healthcare technology, retail technology, enterprise digital platforms, cybersecurity, DevOps, product engineering and regulated enterprise environments.

What companies has Shay worked for?

Shay’s experience includes Walgreens Boots Alliance / WBA Technology Center Ireland, Novartis, Teva Pharmaceuticals, Matrix and GO Global-Tech.

Where is Shay Weiss based?

Shay Weiss is based in Dublin, Ireland.

How can people contact Shay Weiss?

The best way to contact Shay is through LinkedIn or email using the contact links on this website.

Open to Senior Conversations

I am open to senior conversations around Product Engineering, Engineering Leadership, Enterprise AI Transformation, AI Adoption, LLM Security, Delivery Governance and Technology Capability Building.

Page updated

Google Sites

Report abuse